Saddest. Songs. Ever. 2

Here is a devastating list of the saddest songs ever. Contributed by friends and acquaintances. This would be the perfect accompaniment if you were hosting a Cry Party. Or if you were whoopin’ it up with friends and you wanted to bring the mood way the fuck down.

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Mary Chapin Carpenter -I Am A Town

(Contributed by Wes Modes)

Yo La Tengo - Tears Are In Your Eyes

(Contributed by Chris Hirst)

Kilkelly

(Contributed by Andrea Louise Dawson Webster)

Richmond Fontaine - The Janitor

(Contributed by Nydia Cecilia)

Don McLean - American Pie

(Contributed by Wes Modes)

The Decemberists - Eli, the barrow boy

(Contributed by Sean Rbrt)

Raffi - Baby Beluga

(Contributed by Ryan Wade)

The Smiths - I Know It's Over

(Contributed by Rob Simons)

Hurt - NIN (Johnny Cash version).

(Contributed by Fehkor MacFakerson)

T.B. Sheets - Van Morrison

(Contributed by Joe Williams)

Diamanda Galas - Gloomy Sunday

(Contributed by Margaret Kiljoy)

Nick Cave And The Bad Seeds - She Fell Away

(Contributed by Margaret Kiljoy)

Tomorrow Is A Long Time - Bob Dylan (Original Version)
http://www.youtube.com/watch?v=-N9Kg6DqGfc
(Contributed by Marisa Villarreal)

Judy Garland - Over The Rainbow (as Hobo)

(Contributed by Jacob Garbe)

Simon and Garfunkel - Bridge Over Troubled Water

(Contributed by Marisa Villarreal)

Tim Hardin - Hang on to a Dream

(Contributed by Joseph Carter)

How To Disappear Completely

(Contributed by Jacob Garbe)

Gomez - We Haven't Turned Around

(Contributed by Marisa Villarreal)

Terry Jacks - Seasons In The Sun

(Contributed by Tracey Walker)

Glen Hansard - Leave

(Contributed by Marisa Villarreal)

Sam Stone - John Prine

(Contributed by Joe Williams)

Maura O'Connell with Karen Matheson - Down by the Salley Gardens (1998)

(Contributed by Tiffany Jo Waddell)

John Prine - Lake Marie

(Contributed by Wes Modes)

Nirvana - Where did you sleep last night - Unplugged in new york

(Contributed by Jennifer Fleming)

Chumbawamba - By and By

(Contributed by Joe Williams)

Joy Division - Love Will Tear Us Apart

(Contributed by Jennifer Fleming)

Jim Croce - Operator (Live)

(Contributed by Wes Modes)

Redford (for Yia-Yia & Pappou) - Michigan, 14/15

(Contributed by Marisa Villarreal)

Greg Laswell - And Then You

(Contributed by Julie Anna Teague)

The Replacements - Unsatisfied
http://www.youtube.com/watch?v=ub75Sk1Wrcc
(Contributed by Marisa Villarreal)

The Replacements - Achin' to Be

(Contributed by Marisa Villarreal)

Sufjan Stevens - Casimir Pulaski Day

(Contributed by Julie Anna Teague)

Bon Iver & St. Vincent - Roslyn

(Contributed by Marisa Villarreal)

Linda Perry & Grace slick - Knock Me Out

(Contributed by Joe Williams)

Carmen Mcrae Miss Otis Regrets 1980

(Contributed by Joe Williams)

White Lion - When the Children Cry

(Contributed by Joe Williams)

Kris Kristofferson - Casey's Last Ride

(Contributed by David Seaman)

Elliot Smith - King's Crossing

(Contributed by Finn Arak)

Rod Stewart - The Killing of Georgie (Part I and II)

(Contributed by Wallace Baine)

Star Anna & The Laughing Dogs - Alone In This Together (Live on KEXP)

(Contributed by David Seaman)

The Great Lake Swimmers - Changing Colours

(Contributed by David Seaman)

Our Town - Iris DeMent (H.Q.)

(Contributed by Jeremiah Daniels)

Mazzy Star - Into Dust

(Contributed by Adrian Nankivell)

The Mamas & The Papas - Monday Monday

(Contributed by Add Wilson)

Metallica - One (Official Music Video)

(Contributed by Add Wilson)

Soul Asylum - Runaway Train

(Contributed by Add Wilson)

Upside Drown - Go (at Black Butte Center for Railroad Culture)
http://m.youtube.com/watch?v=xu45mYuEMPQ
(Contributed by Jen Nifer)

Leonard Cohen - I'm your man

(Contributed by Jessica Bender)

Ray LaMontagne- Empty

(Contributed by Mike Parisi)

Leonard Cohen - Dance me to the end of love

(Contributed by Jessica Bender)

Morphine - Gone For Good

(Contributed by Sierra Howard Murphree)

Peter, Paul, And Mary - Puff The Magic Dragon (Live 1965)

(Contributed by Kischka Bluspiro)

Karen Dalton - Katie Cruel

(Contributed by Josefina Rocha)

Björk - Gloomy Sunday.

(Contributed by Joe Williams)

nina simone - strange fruit

(Contributed by Joe Williams)

Sinead O'Connor & Roger Waters - Mother

(Contributed by Joe Williams)

Dr.John & Odetta - Brother Can You Spare a Dime

(Contributed by Joe Williams)

Some Say Leland - Hunchback (Local Live)

(Contributed by Sean Zenobia)

Catherine Wheel - Descending Babe

(Contributed by Mike Parisi)

Des Ark - Peace to you too, motherf*cker

(Contributed by Fennec Oak)

Al Green - How Can You Mend A Broken Heart

(Contributed by Wes Modes)

Ani DiFranco - You Had Time

(Contributed by Wes Modes)

Damien Rice - Older Chests

(Contributed by Jacob Garbe)

Seems so long ago, Nancy - Leonard Cohen

(Contributed by Joe Cantrell)

Tom Waits - Georgia Lee

(Contributed by Wallace Baine)

Anne Briggs - Go Your Way

(Contributed by Jo Isaacson)

Abner Jay - I'm So Depressed

(Contributed by Jo Isaacson)

Ted Hawkins- Sorry You're Sick

(Contributed by Joe Cantrell)

Simon & Garfunkel - The Dangling Conversation

(Contributed by Jeannette Crow)

I Can't Make You Love Me - Bonnie Raitt (1991)
http://www.youtube.com/watch?v=xfwylq9ZDyw
(Contributed by Jeannette Crow)

George Michael - Kissing a Fool

(Contributed by Jeannette Crow)

Low - Weight of Water

(Contributed by Joe Cantrell)

Belle & Sebastian-Beautiful

(Contributed by Joe Cantrell)

Joey+Rory - When I'm Gone

(Contributed by Daniel DeFabio)

Smog - I Break Horses (1999)

(Contributed by Kasey Feral Smith)

Willie and Lukas Nelson - Just Breathe (Pearl Jam cover)

(Contributed by Daniel DeFabio)

Nick Drake- Riverman

(Contributed by Espresso Buzz)

Ooh Child - Beth Orton

(Contributed by Daniel DeFabio)

Roberta Flack - Jesse

(Contributed by Wes Modes)

Big Bird at Jim Henson's Memorial

(Contributed by Dave Dirk and Marisa Villarreal)

One Tin Soldier

(Contributed by Kate Compton)

Harry Nilsson - Without You 1972

(Contributed by Jami Losurdo)

Smoking Popes - Pretty Pathetic

(Contributed by Kenan Sharpe)

If you have more songs, please add them to the comments along with a YouTube link.

2 thoughts on “Saddest. Songs. Ever.

  1. Reply Jana Ducret Dec 16,2013 4:41 pm

    Brad Paisley = Whiskey Lullaby

  2. Reply Thom Dec 21,2013 7:29 pm

    Pierce Pettis — You’re Not There

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